Dimethyl Sulfoxide → HCID 23052519, compound

HRID 1650781Notes

Reaction equation

HRID 1650781 reaction equation
FC(F)(F)[C:3]([O:5][C:6](=O)[C:7](F)(F)F)=O.CS(C)=O.[CH2:18]([O:25][N:26]1[CH2:30][CH:29]([CH2:31][CH3:32])[CH:28](O)[C:27]1=[O:34])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.CO>ClCCl.O>[CH2:18]([O:25][N:26]1[CH2:30][C:29]([CH2:31][CH3:32])=[C:28]([NH:26][CH2:30][C:29]2[CH:31]=[CH:7][C:6]([O:5][CH3:3])=[CH:27][CH:28]=2)[C:27]1=[O:34])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

7

Reactant 4

HCID 679Dimethyl SulfoxideHCID 887MethanolHCID 9845Trifluoroacetic anhydrideHCID 23052512HCID 23052512, compound

Product 1

HCID 23052519HCID 23052519, compoundYield 105%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

Trifluoroacetic anhydride (1.8 ml, 2.6 g, 12.7 mmol) was added dropwise to a solution of dimethylsulphoxide (1 ml, 1.1 g, 16.2 mmol) in dichloromethane (40 ml) at -78° C. After 10 min 1-Benzyloxy-4-ethyl-3-hydroxypyrrolidin-2-one (0.94 g, 4 mmol) in dichloromethane (8 ml) was added, the mixture stirred for 30 min, then ethyldiiscpropylamine (4.5 ml, 3.4 g, 26.3 mmol) added. After 45 min methanol (1 ml) was added and the solution brought to room temperature. Water was added and the mixture extracted with ether (3×75 ml). The combined organic layers were washed with brine, dried (MgSO4), evaporated in vacuo, and the residue dissolved in methanol (10 ml). 4-Methoxybenzylamine (1.1 ml) was added and the solution kept at room temperature overnight. The solvent was then removed in vacuo, and the product purified by flash chromatography, eluting with light petroleum:ethyl acetate (5:2 v/v) to give 1-benzyloxy-4-ethyl-3-(4-methoxybenzylamino)-2-oxo-2,5-dihydropyrrole as an oil (0.74 g, 55%). 1H NMR (250 MHz, CDCl3) δ7.4-7.5 (5 H, m, ph), 7.22 (2 H, d, J=9 Hz, MeOCCH), 6.85 (2 H, d, J=9 Hz, MeCCHCH), 5.02 (2 H, s, OCH2), 4.32 (2 H, s, CH2NH), 3.78 (3 H, s, OMe), 3.60 (2 H, s, CH2NO), 2.22 (2 H, q, J= 7 Hz, CH2CH3), 0.93 (3 H, t, J=7 Hz, CH3), m/z 353 (M+ +H).

Workup

  1. additionethyldiiscpropylamine (4.5 ml, 3.4 g, 26.3 mmol) added
  2. custombrought to room temperature
  3. extractionthe mixture extracted with ether (3×75 ml)
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried (MgSO4)
  6. customevaporated in vacuo
  7. dissolutionthe residue dissolved in methanol (10 ml)
  8. addition4-Methoxybenzylamine (1.1 ml) was added
  9. waitthe solution kept at room temperature overnight
  10. customThe solvent was then removed in vacuo
  11. customthe product purified by flash chromatography
  12. washeluting with light petroleum:ethyl acetate (5:2 v/v)

Sources & evidence

ORD record
ord-95c67fe1bbe543ee8c39a7c3911700e4
Source dataset
uspto-grants-1990_05
Patent number
US04925867

Reaction notes

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